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Heading SouthWest (HSW) is an on-road and off-road unsupported bikepacking adventure across Portugal in one-stage. The seek for the lost essence of cycling. In 2027, bikepackers will cross Portugal from North to South. The sixth edition will start in BRAGANÇA and will finish in the edge of Europe: SAGRES, ALGARVE. Two routes available: the traditional on-road route HEADING SOUTHWEST and the new gravel route TRAVESSIA NACIONAL BIKEPACKING.

HSW'27 20-25 JUNE 2027, PORTUGAL.

ON ROAD x OFF ROAD

book your spot



2027: heading SAGRES

HSW'27 // 20-25 JUNE

​BOOK YOUR SPOT​

THE ROUTE 2026 

From the road cycling paradise and Portuguese Highlands of Serra da Estrela, through the mysterious and surprising lands of Trás-os-Montes, past the castles and historical villages in the borderline with Spain, across the brutal views over Côa river, and along the dramatic slopes of the Douro Valley — the Heading SouthWest journey is as diverse as it is demanding.

Two routes await: HSW 1000 and the new distance HSW 500.

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GUIDELINES 2026

'The hardest line to cross is the starting line'. This page is your compass if you’re planning to join us on June 2026. Heading SouthWest is for riders seeking true adventure — resilient, self-reliant cyclists ready to take on one of the most challenging on-road routes in Southern Europe. Here you’ll find the concept behind HSW, our values and principles and details of the registration.

See you at the starting line, seeking together the essence of cycling.

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What is 'Heading SouthWest'?

Heading SouthWest is simultaneously a personal bikepacking challenge and a collective cycling adventure. An opportunity to face your physical and emotional limits while other adventurers are doing the same. It isn't a race or a competition. 'SouthWest' follows 'self supported' approach and drafting is not allowed.

Route Profile and Time Limit

HSW'26 will start and finish in Guarda. The on-road set route will have 1.000 kilometers and approximately 20.000 meters of elevation gain. Riders will have 6 days to finish. A provisional version of the route will be announced soon.

How to arrive to Guarda?

The closest airports are in Lisbon and Porto. The city of Guarda is integrated into the national train network system and is served by two main national lines: Linha da Beira Alta and Linha Beira Baixa.

What Does 'Self Supported' Mean?

Unsupported ultracycling seeks the essence of cycling through the spirit of adventure, independence, autonomy and equality of circumstances among all participants. It's about your experience and challenging your own limits. So makes no sense to receive help from your family and friends with resupplies, mechanical support and accommodation. You can only use the commercial services available to the public and that are available to all riders. Riders of the 'Touring' category are allowed to help each other.

What Does 'No Drafting' Mean?

Drafting is not allowed: you cannot ride on the wheel of other participants (except your fellow pair), cyclists or vehicles, thus obtaining aerodynamic advantages.

Mandatory Items for Participants

Helmet, reflective vest (nights and poor visibility conditions), frontal and rear lights (including a backup kit), emergency blanket. The organization assures personal insurance for accidents (expenses for treatment, repatriation, disability and death). Presence at the briefing session is mandatory (on Friday June 6th evening).

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